3253-91-6

Upstream product

• 19684-32-3 1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 33985-40-9 (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 
• 29325-28-8 (3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-6-vinyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole 
• 67-56-1 methanol 
• 55085-28-4 5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 77-76-9 2,2-dimethoxy-propane 
• 51168-76-4 2-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)acetaldehyde 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 189165-95-5 6-O-(tert-butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 189165-94-4 (3aR,5R,6S,6aR)-5-<2-(tert-butyldimethylsiloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-ol 
• 189165-93-3 2-(tert-Butyl-dimethyl-silanyloxy)-1-((3aR,5S,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanone 
• 220325-36-0 (3aR,5R,6aR)-5-<2-(tert-butyldimethylsiloxy)ethyl>dihydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6(5H)-one 

Downstream Products

• 189166-01-6 6'-O-nitro-2'-O-tosylhomoadenosine 

Relevant academic research and scientific papers

Synthesis of LuxS inhibitors targeting bacterial cell-cell communication

(Chemical Equation Presented) Quorum sensing is a process by which bacteria sense cell density. This cell-cell communication process is mediated by autoinducers. A cross-species messenger, autoinducer-2 (Al-2) is produced from S-ribosyl-L-homocysteine by the LuxS enzyme. A proposed mechanism for LuxS is an aldose-ketose isomerization of S-ribosylhomocysteine followed by a β-elimination. We report here the synthesis of two substrate analogues, S-anhydroribosyl-L-homocysteine and S-homoribosyl-L-cysteine, which prevent the initial and final step of the mechanism, respectively.

5′-Homoaristeromycin. Synthesis and antiviral activity against orthopox viruses

An efficient synthesis of 5′-homoaristeromycin has been developed. This permitted an extensive antiviral analysis, which found potent activity toward vaccinia, cowpox, and monkeypox viruses. For comparative purposes, 5′-homoadenosine was made available by a newly designed route and found to be inactive.

An Efficient Synthesis of 5-Deoxy-D-ribohexose

5-Deoxy-D-ribohexose (1) has been obtained from methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside via Wittig reaction with methoxymethylenetriphenyl phosphorane and subsequent hydrolytic and deprotection steps. 13C NMR spectrum show, that 1 occurs as two furanoses, two septanoses and an aldehydo form.Peracetylation of 5-deoxy-D-ribohexose leads to both furanose forms and, most probably, to an α-septanose ring.Key words: 5-deoxy-D-ribohexose, Wittig reaction